This proposal describes the preparation of new molecules that hold promise as DNA cleaving agents. All the molecules being proposed possess one common feature, they contain a [3]cumulene moiety along with an array of conjugated double and triple bonds. Cumulenes have been postulated as reactive intermediates in the triggering mechanism of Neocarzinostatin chromophore (and analogs), one of the most potent naturally occurring DNA cleaving agent known. The work being proposed is an attempt to put to practical use a new process discovered in these laboratories, the preparation of functionalized [3]cumulenes. The new reaction was proposed in a previous NIH-MBRS proposal and consists of a Lewis acid induced rearrangement/dehydration of epoxy alkynols to [3]cumulenes and hydroxy allenes. This reaction will be exploited for the synthesis of several [3]cumulenes possessing the structural features capable of undergoing Bergman/Meyers type cycloaromatization to afford diradical intermediates (the species responsible for DNA cleaving activity). After the proposed molecules have been synthesized, provisions have been made to test out the effectiveness as DNA cleaving agents via gel electrophoresis techniques.